Methyl 3-oxovalerate → HCID 57466732, Verbindung

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].C[O-].[Na+].O/[N:14]=[C:15](\Cl)/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH3:1][O:2][C:3]([C:4]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:14][O:8][C:5]=1[CH2:6][CH3:7])=[O:9]

Komponenten

Versuchsvorschrift

To a solution of 3-oxo-pentanoic acid methyl ester (19.3 g, 0.15 mol) in methanol (30 mL) was added a solution of sodium methoxide (8.1 g, 0.15 mol) in methanol (30 mL) dropwise under ice-bath cooling keeping the temperature below 30° C. The reaction mixture was then stirred at room temperature for 30 min. Then a solution of (E)- and/or (Z)-N-hydroxy-benzenecarboximidoyl chloride (21.7 g, 0.14 mol, in Example 1a) in methanol (78 mL) was added to this mixture under ice-bath cooling keeping the temperature below 0° C. After adding, the ice-bath was removed and stirring was continued overnight at room temperature. The resulting mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The aqueous phase was further extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulphate and concentrated to give the title compound as a yellow oil which was used in the next reaction without further purification. MS: m/e=232.1 [M+H]+.